Record Information |
---|
Version | 1.0 |
---|
Creation date | 2011-09-21 00:11:18 UTC |
---|
Update date | 2015-07-21 06:57:07 UTC |
---|
Primary ID | FDB022271 |
---|
Secondary Accession Numbers | |
---|
Chemical Information |
---|
FooDB Name | Neuraminic acid |
---|
Description | Neuraminic acids are the commonest sialic acids in nature. Most sialic acids on gangliosides share a core neuraminic acid (Neu) structure and are N-acylated at the C-5 position with either an N-acetyl or an N-glycolyl group (giving Neu5Ac or Neu5Gc, respectively). It was originally thought that unsubstituted glycosidically linked Neu did not occur in nature. However, there have been several reports suggesting its presence in gangliosides and more recently in mucin-type glycoproteins. The N- or O-substituted derivatives of neuraminic acid are collectively known as sialic acids, the predominant one being N-acetylneuraminic acid. The amino group bears either an acetyl or a glycolyl group. The hydroxyl substituents may vary considerably: acetyl, lactyl, methyl, sulfate and phosphate groups have been found. Sialic acids are found widely distributed in animal tissues. Sialic acid rich glycoproteins bind selectin in humans and other organisms. Cancer cells that can metastasize often have a lot of sialic acid rich glycoproteins. This helps these late stage cancer cells enter the blood stream. (PMID: 11884388) [HMDB] |
---|
CAS Number | 114-04-5 |
---|
Structure | |
---|
Synonyms | Synonym | Source |
---|
Neuraminate | Generator | 5-(Acetylamino)-3,5-dideoxy-beta-L-erythro-2-nonulopyranosonate | HMDB | 5-(Acetylamino)-3,5-dideoxy-beta-L-erythro-2-nonulopyranosonic acid | HMDB | O-Sialate | HMDB | O-Sialic acid | HMDB | b-Neuraminate | HMDB | b-Neuraminic acid | HMDB | beta-Neuraminate | HMDB | Β-neuraminate | HMDB | Β-neuraminic acid | HMDB | 5-(acetylamino)-3,5-dideoxy-beta-L-erythro-2-nonulopyranosonate | hmdb | 5-(acetylamino)-3,5-dideoxy-beta-L-erythro-2-nonulopyranosonic acid | hmdb | O-sialate | hmdb |
|
---|
Predicted Properties | |
---|
Chemical Formula | C9H17NO8 |
---|
IUPAC name | (2S,4S,5R,6R)-5-amino-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid |
---|
InChI Identifier | InChI=1S/C9H17NO8/c10-5-3(12)1-9(17,8(15)16)18-7(5)6(14)4(13)2-11/h3-7,11-14,17H,1-2,10H2,(H,15,16)/t3-,4+,5+,6+,7+,9-/m0/s1 |
---|
InChI Key | CERZMXAJYMMUDR-YOQZMRDMSA-N |
---|
Isomeric SMILES | N[C@@H]1[C@@H](O)C[C@](O)(O[C@H]1[C@H](O)[C@H](O)CO)C(O)=O |
---|
Average Molecular Weight | 267.2332 |
---|
Monoisotopic Molecular Weight | 267.095416525 |
---|
Classification |
---|
Description | Belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Fatty Acyls |
---|
Sub Class | Fatty acid esters |
---|
Direct Parent | Acyl carnitines |
---|
Alternative Parents | |
---|
Substituents | - Acyl-carnitine
- Dicarboxylic acid or derivatives
- Tetraalkylammonium salt
- Quaternary ammonium salt
- Carboxylic acid ester
- Carboxylic acid salt
- Carboxylic acid derivative
- Carboxylic acid
- Organic nitrogen compound
- Organooxygen compound
- Organonitrogen compound
- Organic salt
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Carbonyl group
- Amine
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Physiological effect | Health effect: |
---|
Disposition | Source: Biological location: |
---|
Physico-Chemical Properties |
---|
Physico-Chemical Properties - Experimental | Property | Value | Reference |
---|
Physical state | Solid | |
---|
Physical Description | Not Available | |
---|
Mass Composition | Not Available | |
---|
Melting Point | Not Available | |
---|
Boiling Point | Not Available | |
---|
Experimental Water Solubility | Not Available | |
---|
Experimental logP | Not Available | |
---|
Experimental pKa | Not Available | |
---|
Isoelectric point | Not Available | |
---|
Charge | Not Available | |
---|
Optical Rotation | Not Available | |
---|
Spectroscopic UV Data | Not Available | |
---|
Density | Not Available | |
---|
Refractive Index | Not Available | |
---|
|
---|
Spectra |
---|
Spectra | |
---|
EI-MS/GC-MS | Type | Description | Splash Key | View |
---|
Predicted GC-MS | Neuraminic-acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-08i3-9120000000-3c41863dc43e1c340e0c | Spectrum | Predicted GC-MS | Neuraminic-acid, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-03dl-9050317000-14973db7ffcbfc34052e | Spectrum | Predicted GC-MS | Neuraminic-acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neuraminic-acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neuraminic-acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neuraminic-acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neuraminic-acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neuraminic-acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neuraminic-acid, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neuraminic-acid, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neuraminic-acid, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neuraminic-acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neuraminic-acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neuraminic-acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neuraminic-acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neuraminic-acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neuraminic-acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neuraminic-acid, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neuraminic-acid, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neuraminic-acid, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neuraminic-acid, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neuraminic-acid, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neuraminic-acid, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neuraminic-acid, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neuraminic-acid, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
|
---|
MS/MS | Type | Description | Splash Key | View |
---|
Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0uxr-0090000000-d89dc6b36e86f946452e | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03e9-9750000000-2aed2f62b96aad393b88 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03dl-9210000000-97dc8f0546cc39db3750 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0wna-5960000000-b190e5b95aab09e21fd3 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-9300000000-716acbc025a479fc33f7 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9200000000-83bec5b63a8ab9d103cf | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-3190000000-f2d299e55cb15d9bd7f3 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-052r-9220000000-af4f3586fa7d7a2ccaf9 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052o-9000000000-fbd3594b908b216886e6 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0090000000-4868512633217955d5ba | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0fur-3960000000-6a998b7b483922ea5dc8 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0200-9400000000-eb39b86e7545b7da59f6 | 2021-09-22 | View Spectrum |
|
---|
NMR | Not Available |
---|
External Links |
---|
ChemSpider ID | 447972 |
---|
ChEMBL ID | Not Available |
---|
KEGG Compound ID | C06469 |
---|
Pubchem Compound ID | 513472 |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | 27851 |
---|
Phenol-Explorer ID | Not Available |
---|
DrugBank ID | Not Available |
---|
HMDB ID | HMDB00830 |
---|
CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
---|
EAFUS ID | Not Available |
---|
Dr. Duke ID | Not Available |
---|
BIGG ID | Not Available |
---|
KNApSAcK ID | Not Available |
---|
HET ID | Not Available |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
Flavornet ID | Not Available |
---|
GoodScent ID | Not Available |
---|
SuperScent ID | Not Available |
---|
Wikipedia ID | Neuraminic acid |
---|
Phenol-Explorer Metabolite ID | Not Available |
---|
Duplicate IDS | Not Available |
---|
Old DFC IDS | Not Available |
---|
Associated Foods |
---|
Food | Content Range | Average | Reference |
---|
Food | | | Reference |
---|
|
Biological Effects and Interactions |
---|
Health Effects / Bioactivities | Not Available |
---|
Enzymes | Name | Gene Name | UniProt ID |
---|
Bifunctional UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase | GNE | Q9Y223 |
|
---|
Pathways | Not Available |
---|
Metabolism | Not Available |
---|
Biosynthesis | Not Available |
---|
Organoleptic Properties |
---|
Flavours | Not Available |
---|
Files |
---|
MSDS | Not Available |
---|
References |
---|
Synthesis Reference | Not Available |
---|
General Reference | Not Available |
---|
Content Reference | |
---|